Diisobutylaluminumhydride → 2-(Methylthio)benzo[d]oxazole-6-methanol

Temperature

-30 °C

To a stirred solution of methyl 2-(methylthio)benzo[d]oxazole-6-carboxylate (4.24 g, 19 mmol) from Step 1 of this Example in anhydrous DCM (100 mL) under an argon atmosphere at −78° C. was added dropwise diisobutylaluminum hydride (1.0 M solution in DCM, 40 mL, 40 mmol). The mixture was allowed to warm to −30° C. over 2 h. The reaction was quenched by addition of saturated aq sodium potassium tartrate and the resulting mixture stirred at rt for an additional 15 h. The organic layer was separated and the aqueous layer extracted with additional DCM (×2). The combined organic layers were washed with water dried over MgSO4, filtered, and concentrated under reduced pressure to afford (2-(methylthio)benzo[d]oxazol-6-yl)methanol (2 g, 54%) as a tan solid that did not require further purification. 1H NMR (300 MHz, DMSO-d6) δ 7.51-7.61 (m, 2H), 7.28 (d, J=8.3 Hz, 1H), 5.34 (t, J=5.7 Hz, 1H), 4.59 (d, J=5.7 Hz, 2H), 2.76 (s, 3H). LCMS (ESI) m/z 196 (M+H)+.

1. customat −78° C.
2. customThe reaction was quenched by addition of saturated aq sodium potassium tartrate
3. customThe organic layer was separated
4. extractionthe aqueous layer extracted with additional DCM (×2)
5. washThe combined organic layers were washed with water
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-0543c1eec343427da5a9e3106fd8801f

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952058B2